Unusual Rearrangement by Anodic Oxidation of Cycloalkanones in the Presence of Trifluoroacetic Acid

  • Ikuzo Nishiguchi
Conference paper


Anodic oxidation of cyclopentanone and cyclohexanones in a mixed solvent of CF3COOH and CH2C12 containing triethylamine led to unusual rearrangement to give selectively γ-valerolactone and a mixture of γ-and δ-lactones, respectively.

Anodic cleavage of a bond between the carbonyl carbon and the adjacent carbon of cycloalkanones followed by Wagner-Meerwein rearrangement and re-cyclization may be proposed as one of the most plausible reaction mechanisms.


Anodic Oxidation Carbonyl Carbon Lithium Perchlorate Sole Product Cyclic Ketone 
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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Ikuzo Nishiguchi
    • 1
  1. 1.Department of ChemistryNagaoka University of TechnologyNagaoka, NiigataJapan

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